Ethyl orthoformate → 3-(3-Methoxypropyl)-2-thioxanthine

HRID 31062Notes

Reaction equation

HRID 31062 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH2:10][O:11][CH3:12])[C:6](=[S:13])[NH:5][C:4](=[O:14])[C:3]=1[N:15]=O.N[C:18]1C(=O)NC(=S)N(CC2CCCCC2)C=1N.C(OCC)(OCC)OCC>[Pt].O1CCCC1.O.C(O)C>[CH3:12][O:11][CH2:10][CH2:9][CH2:8][N:7]1[C:2]2[N:1]=[CH:18][NH:15][C:3]=2[C:4](=[O:14])[NH:5][C:6]1=[S:13]

Participants

8

Reactant 3

HCID 31214Ethyl orthoformateHCID 86601053HCID 86601053, compoundHCID 866010546-amino-1-(3-methoxypropyl)-5-nitroso 2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

Product 1

HCID 103542623-(3-Methoxypropyl)-2-thioxanthineYield 9%

Reagents, catalysts & solvents 4

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Platinum on carbon (0.5 g) was added to a solution of the crude 6-amino-1-(3-methoxypropyl)-5-nitroso 2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (1.80 g, 7.38 mmol) in tetrahydrofuran (80 mL) and water (20 mL) and the reaction mixture was hydrogenated at atmospheric pressure for 2 h. The catalyst was filtered off and the pale brown filtrate was co-evaporated with ethanol (250 mL). The resulting brown solid, 1.6 g, was used in the next step without further purification. 5,6-Diamino-1-cyclohexylmethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (1.6 g, 12.2 mmol) was dissolved in ethanol (10 mL) and triethyl orthoformate (10 mL) and the reaction mixture was refluxed for 2.5 h. The solvents were evaporated off and the resulting brown solid was purified by flash chromatography (heptane/ethyl acetate, 4:1-1:1) to give the title compound (110 mg, 9%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customThe resulting brown solid, 1.6 g, was used in the next step without further purification
  3. customThe solvents were evaporated off
  4. customthe resulting brown solid was purified by flash chromatography (heptane/ethyl acetate, 4:1-1:1)

Sources & evidence

ORD record
ord-46148c5d93db4dbaa282d7a294d07ddc
Source dataset
uspto-grants-2008_09
Patent number
US07425560B2

Reaction notes

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